Stereoselective Total Synthesis of (-)-Renieramycin T

J Org Chem. 2016 May 20;81(10):4039-47. doi: 10.1021/acs.joc.6b00327. Epub 2016 May 3.

Abstract

A stereoselective total synthesis of (-)-Renieramycin T (1t) from a key tetrahydroisoquinoline intermediate previously utilized in our formal total synthesis of Ecteinascidin 743 is described. The synthesis features a concise approach for construction of the pentacyclic framework using a Pictet-Spengler cyclization of bromo-substituted carbinolamine 17, which obviates the regioselectivity problem of the Pictet-Spengler cyclization. The results of cytotoxicity studies are also presented.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Hydrogen-Ion Concentration*
  • Magnetic Resonance Spectroscopy
  • Stereoisomerism
  • Tetrahydroisoquinolines / chemical synthesis*

Substances

  • Tetrahydroisoquinolines
  • renieramycin T